448-61-3

Usage

Uses

Used in Photochemical Applications:
2,4,6-Triphenylpyrylium tetrafluoroborate is used as a sensitizer for the photooxidation of catechol. It serves as a catalyst to initiate the reaction, enhancing the efficiency of the process and allowing for the conversion of catechol into more valuable products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4,6-triphenylpyrylium tetrafluoroborate is used in the preparation of three N-alkylpyridinium photosensitizers. These photosensitizers are synthesized by reacting the compound with (1R,2S)-(-)-norephedrine, (S)-(+)-2-(aminomethyl)pyrrolidine, and (R)-(-)-1-cyclohexylethylamine. These photosensitizers have potential applications in photodynamic therapy, a treatment method that uses light to activate a drug, which then kills cancer cells.
Used in Chemical Synthesis:
2,4,6-Triphenylpyrylium tetrafluoroborate is also used as a starting material or intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable building block for the development of new molecules with specific properties and applications.
Used in Research and Development:
Due to its photochemical properties, 2,4,6-triphenylpyrylium tetrafluoroborate is often utilized in research and development for studying the fundamental aspects of photochemistry and photophysics. It can be employed to investigate the mechanisms of light-induced reactions and to develop new strategies for controlling the behavior of molecules under the influence of light.

InChI:InChI=1/C23H17O.BF4/c1-4-10-18(11-5-1)21-16-22(19-12-6-2-7-13-19)24-23(17-21)20-14-8-3-9-15-20;2-1(3,4)5/h1-17H;/q+1;-1

Upstream product

• 455-32-3 benzoyl fluoride 
• 54435-79-9 (E)-1,3-diphenyl-3-methyl-2-propen-1-one 
• 109-63-7 trifluoroborane diethyl ether 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 40836-01-9 2,4,6-triphenylpyrylium chlorophosphate 
• 94-41-7 benzalacetophenone 
• 536-74-3 phenylacetylene 
• 109-63-7 boron trifluoride diethyl etherate 
• 67969-82-8 tetrafluoroboric acid diethyl ether 

Downstream Products

• 1177-69-1 2-benzyl-2,4,6-triphenyl-2H-pyran 
• 10368-47-5 2-nitro-1,3,5-triphenyl-benzene 
• 121677-01-8 6'-benzoyl-5'-hydroxy-m-terphenyl-4'-carboxylic acid ethyl ester 
• 23800-57-9 1,3,5-triphenylpent-2-en-1,5-dione 
• 580-35-8 2,4,6-triphenylpyridine 
• 79196-50-2 2,4-diphenyl-5-benzoyl-6-aminobenzonitrile 
• 3140-01-0 2,4,6-triphenylphenol 
• 40252-57-1 C₃₇H₂₅NO₄ 
• 40252-14-0 C₃₇H₂₆O₃ 
• 56444-37-2 (4-phenylisoxazole-3,5-diyl)bis(phenylmethanone) 
• 70336-74-2 2,5,7-triphenyl-[1,3]oxazepine 
• 31860-56-7 2-(3,5-diphenyl-4,5-dihydro-isoxazol-5-yl)-1-phenyl-ethanone oxime 
• 13497-36-4 2,4,6-triphenylphosphinine 
• 96972-25-7 C₄₄H₃₅O₃P 

Relevant academic research and scientific papers

On the Electron-Donating Properties of Oxygen vs. Sulfur. Redox Potentials for Some Pyrylium and Thiapyrylium Salts

The redox levels for two series of pyrylium and thiapyrylium salts were measured by cyclic voltammetry.This information was utilized to provide a quantitative comparison of the highest occupied (HOMO) and lowest unoccupied molecular orbitals (LUMO) which is a measure of the thermodynamic stabilities to electron transfer of oxygen vs. sulfur adjacent to carbon cation, radical, and anionic centers in a single system.In one of the series dicationic, cationic, radical, and anionic centers were compared.The ionic and radical species were found to be thermodynamically more stable in the sulfur analogue (less stable in oxygen analogue) in every case except when the HOMO and/or LUMO level is localized on the diethylaminophenyl moiety.The order of the greatest sulfur preference or least oxygen preference is the following: anion>radical and radical>cation for the HOMO and LOMO levels, respectively.The wavelength of the intramolecular charge transfer band and the electrochemical reduction potentials indicate that the thiapyrylium moiety is more electron withdrawing than pyrylium.

Radical alkylation of isocyanides with amino acid-/peptide-derived Katritzky salts via photoredox catalysis

An efficient and mild method was developed for the synthesis of 6-alkylated phenanthridines upon visible light irradiation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amino acids/peptides were used as radical precursors for the alkylation of isocyanobiphenyl species. The reaction displays an excellent functional group tolerance and a potential utility for peptide functionalization, allowing access to desired products in good to excellent yields.

4-Benchrotrenyl pyrylium salts as protein organometallic labelling reagents

Pyrylium ions are useful reagents to selectively modify the amino group of protein lysine residues. This property was exploited here to label proteins with chromium tricarbonyl complexes in the form of 4-benchrotrenyl pyridinium ions. Kinetic studies of the reaction of a series of benchrotrenyl pyrylium salts with water and n-butylamine were performed and revealed that the overall reactivity of these compounds was highly dependent on their substitution pattern. These compounds could find application in protein X-ray crystallography.

Dissection of alkylpyridinium structures to understand deamination reactions

Via conversion to Katritzky pyridinium salts, alkyl amines can now be used as alkyl radical precursors for a range of deaminative functionalization reactions. The key step of all of these methods is single-electron reduction of the pyridinium ring, which triggers C-N bond cleavage. However, little has been done to understand how the precise nature of the pyridinium influences these events. Using a combination of synthesis, computation, and electrochemistry, this study delineates the steric and electronic effects that substituents have on the canonical steps and the overall process. Depending on the approach taken, consideration of both the reduction and the subsequent radical dissociation may be necessary. Whereas the electronic effects on these steps work in opposition to each other, the steric effects are synergistic, with larger substituents favoring both steps. This understanding provides a framework for future design of pyridinium salts to match the mode of catalysis or activation.

Ruthenium-catalysedmeta-selective CAr-H bond alkylationviaa deaminative strategy

The use of aliphatic amines as alkylating reagents in organic synthesisviaC-N bond activation remains underdeveloped. We herein describe a novel ruthenium-catalysed and directing-group assisted protocol for the synthesis ofmeta-alkylated arenesviadual C-H and C-N activation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amines and amino acid species were used as alkyl radical precursors. This catalytic reaction could accommodate a broad range of functional groups and provide access to variousmeta-alkylated products.

Continuous-Flow Synthesis of Pyrylium Tetrafluoroborates: Application to Synthesis of Katritzky Salts and Photoinduced Cationic RAFT Polymerization

Katritzky salts have emerged as effective alkyl radical sources upon metal- or photocatalysis. These are typically prepared from the corresponding triarylpyrylium ions, in turn an important class of photocatalysts for small molecules synthesis and photopolymerization. Here, a flow method for the rapid synthesis of both pyrylium and Katrizky salts in a telescoped fashion is reported. Moreover, several pyrylium salts were tested in the photoinduced RAFT polymerization of vinyl ethers under flow and batch conditions.

Synthesis method of 2, 4, 6-triphenylpyran tetrafluoroborate

The invention discloses a synthesis method of 2, 4, 6-triphenylpyran tetrafluoroborate, and relates to the technical field of photoelectric materials. The synthesis method comprises the following steps that benzaldehyde and acetophenone are mixed and stirred, the reaction temperature is controlled to range from 15 DEG C to 25 DEG C, boron trifluoride diethyl etherate is dropwise added into a reaction system, the temperature is increased to 50 DEG C to 80 DEG C after dropwise adding is completed, a reaction is conducted for 15 h, when the reaction liquid is cooled to 40 DEG C, the reaction liquid is injected into ethyl acetate under stirring, a yellow solid is separated out, and filtered and purified so as to obtain 2, 4, 6-triphenylpyran tetrafluoroborate; the molar ratio of benzaldehyde to acetophenone is 1: 3, and the mass ratio of boron trifluoride diethyl etherate to acetophenone is 9: 11. The method has the beneficial effects that the 2, 4, 6-triphenylpyran tetrafluoroborate is synthesized by adopting a one-pot method, the synthesis method is simple, the product yield is high, the purity is high, and the industrialization of the product is easy to realize.

C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis

Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.

Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts

A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary alkyl and allyl groups were also successfully introduced via the same method. Additionally, the typically applied N-phenyl group in the THIQ substrate could be replaced by the cleavable p-methoxyphenyl (PMP) group and successful N-deprotection was demonstrated.

Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage

The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.